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Winter Park Homes For Sale & Real Estate - 214 homes

Winter Park homes for sale are located in Orange County, Florida. Find homes in Winter Park for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Winter Park houses.

Location: Winter Park

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  • 688 BRECHIN DRIVE, WINTER PARK, FL 32792

    $434,000Listed 01/15/2021 2:33PM   MLS ID: O5917091

    For Sale O5917091 - 688 BRECHIN DRIVE, WINTER PARK, FL 32792 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1599
       Built: 1961   Tax: $2,544 (2020)
    Community: Kenilworth Shores Sec 04
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,590 (change assumption)
    Mortgage ($2,378) + Taxes in 2020 ($212)

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    Taxes:$2,544

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Glenridge Middle


  • 429 S RANGER BOULEVARD, WINTER PARK, FL 32792

    $359,000186 Days on yellowkey   MLS ID: O5879257

    18 Days Off yellowkey (back on 1/15/2021)

    REDUCED by $16,000 (4.3%) on 01/15/2021

    For Sale O5879257 - 429 S RANGER BOULEVARD, WINTER PARK, FL 32792 16 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1652
       Built: 1965   Tax: $1,712 (2019)
    Community: Winter Park Pines
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,110 (change assumption)
    Mortgage ($1,967) + Taxes in 2019 ($143)

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    Taxes:$1,712

    Elementary School: Aloma Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 1552 FLORENTINO LANE, WINTER PARK, FL 32792

    $285,000Listed 01/14/2021 11:59PM   MLS ID: O5916946

    For Sale O5916946 - 1552 FLORENTINO LANE, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $155
       Tax: $1,186 (2020)
    Community: Vistas At Lake Howell
    Pool: No

    Townhouse


    Estimated Monthly Payment: $1,815 (change assumption)
    Mortgage ($1,562) + Fees ($155) + Taxes in 2020 ($99)

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    Taxes:$1,186

    Elementary School: Sterling Park Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 1935 AZALEA AVENUE, WINTER PARK, FL 32792

    $270,000Listed 01/14/2021 11:59PM   MLS ID: O5917036

    For Sale O5917036 - 1935 AZALEA AVENUE, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1300
       Built: 1954   Tax: $2,335 (2020)
    Community: Temple Terrace Annex
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,674 (change assumption)
    Mortgage ($1,479) + Taxes in 2020 ($195)

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    Taxes:$2,335

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 467 CAROLINA AVENUE, WINTER PARK, FL 32789

    $1,195,000Listed 01/14/2021 10:39PM   MLS ID: O5917041

    For Sale O5917041 - 467 CAROLINA AVENUE, WINTER PARK, FL 32789 34 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 2710
       Built: 2020   Tax: $2,908 (2020)
    Community: Winter Park
    Pool: No

    Single Family


    Estimated Monthly Payment: $6,790 (change assumption)
    Mortgage ($6,548) + Taxes in 2020 ($242)

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    Taxes:$2,908

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1250 S DENNING DRIVE UNIT 128, WINTER PARK, FL 32789

    $199,90053 Days on yellowkey   MLS ID: O5907643

    REDUCED by $10,000 (4.8%) on 01/15/2021

    For Sale O5907643 - 1250 S DENNING DRIVE UNIT 128, WINTER PARK, FL 32789 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 884
       Built: 1967   Tax: $1,749 (2020)
    Community: Mead Garden
    Pool: No

    Condo


    Estimated Monthly Payment: $1,241 (change assumption)
    Mortgage ($1,095) + Taxes in 2020 ($146)

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    Taxes:$1,749

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 2685 GALLIANO CIRCLE, WINTER PARK, FL 32792

    $262,00030 Days on yellowkey   MLS ID: O5912038

    REDUCED by $5,000 (1.9%) on 01/14/2021

    For Sale O5912038 - 2685 GALLIANO CIRCLE, WINTER PARK, FL 32792 25 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1682
       Built: 2004
    Monthly Fee: $155
       Tax: $1,932 (2019)
    Community: Vistas At Lake Howell
    Pool: No

    Townhouse


    Estimated Monthly Payment: $1,752 (change assumption)
    Mortgage ($1,436) + Fees ($155) + Taxes in 2019 ($161)

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    Taxes:$1,932

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 200 SAINT ANDREWS BOULEVARD UNIT 412, WINTER PARK, FL 32792

    $139,9001 Day on yellowkey   MLS ID: O5916746

    For Sale O5916746 - 200 SAINT ANDREWS BOULEVARD UNIT 412, WINTER PARK, FL 32792 41 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 835
       Built: 1970
    Monthly Fee: $310
       Tax: $1,565 (2020)
    Community: Four Seasons Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $1,207 (change assumption)
    Mortgage ($767) + Fees ($310) + Taxes in 2020 ($130)

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    Taxes:$1,565

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 2218 VIA TUSCANY, WINTER PARK, FL 32789

    $2,500,0001 Day on yellowkey   MLS ID: O5915531

    For Sale O5915531 - 2218 VIA TUSCANY, WINTER PARK, FL 32789 88 photos

    Bed: 5   Bath: 6.0
    Liv Area Sq Ft: 4423
       Built: 2020   Tax: $7,250 (2020)
    Community: Tuscany Terrace
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $14,302 (change assumption)
    Mortgage ($13,698) + Taxes in 2020 ($604)

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    Taxes:$7,250

    Elementary School: Dommerich Elem

    High School: Winter Park High

    Tax Year: 2020

    Middle School: Maitland Middle


  • 2687 MERRIE OAKS ROAD, WINTER PARK, FL 32792

    $429,90037 Days on yellowkey   MLS ID: O5910713

    REDUCED by $10,000 (2.3%) on 01/14/2021

    For Sale O5910713 - 2687 MERRIE OAKS ROAD, WINTER PARK, FL 32792 26 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1921
       Built: 1966   Tax: $4,715 (2019)
    Community: Winter Park Pines Merrie Oaks
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $2,748 (change assumption)
    Mortgage ($2,356) + Taxes in 2019 ($393)

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    Taxes:$4,715

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 510 LANDER ROAD, WINTER PARK, FL 32792

    $284,90054 Days on yellowkey   MLS ID: O5907675

    25 Days Off yellowkey (back on 1/12/2021)

    REDUCED by $9,000 (3.1%) on 01/14/2021

    For Sale O5907675 - 510 LANDER ROAD, WINTER PARK, FL 32792 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1368
       Built: 1974   Tax: $3,568 (2019)
    Community: Eastgate Sub
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,858 (change assumption)
    Mortgage ($1,561) + Taxes in 2019 ($297)

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    Taxes:$3,568

    Elementary School: None

    High School: None

    Tax Year: 2019

    Middle School: None


  • 753 JULIAN STREET, WINTER PARK, FL 32789

    $275,0001 Day on yellowkey   MLS ID: O5916643

    For Sale O5916643 - 753 JULIAN STREET, WINTER PARK, FL 32789 20 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 972
       Built: 1952   Tax: $1,551 (2020)
    Community: Dubsdread Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,636 (change assumption)
    Mortgage ($1,507) + Taxes in 2020 ($129)

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    Taxes:$1,551

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1004 LAKE BELL DRIVE, WINTER PARK, FL 32789

    $309,90044 Days on yellowkey   MLS ID: O5909337

    2 Days Off yellowkey (back on 1/14/2021)

    REDUCED by $3,000 (1.0%) on 01/08/2021

    For Sale O5909337 - 1004 LAKE BELL DRIVE, WINTER PARK, FL 32789 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1387
       Built: 1956   Tax: $2,881 (2019)
    Community: Albert Lee Ridge Add 02
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,938 (change assumption)
    Mortgage ($1,698) + Taxes in 2019 ($240)

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    Taxes:$2,881

    Elementary School: Hungerford Elem

    High School: Edgewater High

    Tax Year: 2019

    Middle School: College Park Middle


  • 1000 S SEMORAN BOULEVARD UNIT 110, WINTER PARK, FL 32792

    $122,50042 Days on yellowkey   MLS ID: O5908862

    6 Days Off yellowkey (back on 1/14/2021)

    For Sale O5908862 - 1000 S SEMORAN BOULEVARD UNIT 110, WINTER PARK, FL 32792 13 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1049
       Built: 1969   Tax: $1,254 (2019)
    Community: Golfside Villas Condo
    Pool: No

    Condo


    Estimated Monthly Payment: $776 (change assumption)
    Mortgage ($671) + Taxes in 2019 ($105)

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    Taxes:$1,254

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 1721 SHASTA COURT, WINTER PARK, FL 32792

    $329,9001 Day on yellowkey   MLS ID: O5915975

    For Sale O5915975 - 1721 SHASTA COURT, WINTER PARK, FL 32792 49 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1525
       Built: 1979   Tax: $1,719 (2020)
    Community: Garden Lake Estates Unit 1
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $1,951 (change assumption)
    Mortgage ($1,808) + Taxes in 2020 ($143)

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    Taxes:$1,719

    Elementary School: Red Bug Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 3651 OAK VISTA LANE, WINTER PARK, FL 32792

    $339,0001 Day on yellowkey   MLS ID: O5916432

    For Sale O5916432 - 3651 OAK VISTA LANE, WINTER PARK, FL 32792 23 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1956
       Built: 1981   Tax: $1,378 (2020)
    Community: Garden Lake Estates Unit 2
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,972 (change assumption)
    Mortgage ($1,857) + Taxes in 2020 ($115)

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    Taxes:$1,378

    Elementary School: None

    High School: None

    Tax Year: 2020

    Middle School: None


  • 1166 OXFORD ROAD, WINTER PARK, FL 32789

    $869,500172 Days on yellowkey   MLS ID: O5876647

    27 Days Off yellowkey (back on 1/14/2021)

    INCREASED by $500 (0.1%) on 01/14/2021

    For Sale O5876647 - 1166 OXFORD ROAD, WINTER PARK, FL 32789 35 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3764
       Built: 1947   Tax: $4,448 (2019)
    Community: Virginia Heights
    Pool: No

    Single Family


    Estimated Monthly Payment: $5,135 (change assumption)
    Mortgage ($4,764) + Taxes in 2019 ($371)

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    Taxes:$4,448

    Elementary School: Brookshire Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 1310 ALOMA AVENUE, WINTER PARK, FL 32789

    $738,00037 Days on yellowkey   MLS ID: O5910681

    REDUCED by $10,000 (1.3%) on 01/14/2021

    For Sale O5910681 - 1310 ALOMA AVENUE, WINTER PARK, FL 32789 25 photos

    Bed: 4   Bath: 2.5
    Liv Area Sq Ft: 2623
       Built: 1926   Tax: $3,557 (2019)
    Community: Sylvan Lake Shores
    Pool: No

    Single Family


    Estimated Monthly Payment: $4,340 (change assumption)
    Mortgage ($4,044) + Taxes in 2019 ($296)

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    Taxes:$3,557

    Elementary School: Lakemont Elem

    High School: Winter Park High

    Tax Year: 2019

    Middle School: Glenridge Middle


  • 1004 SHEFFIELD COURT, WINTER PARK, FL 32792

    $324,2001 Day on yellowkey   MLS ID: O5916792

    For Sale O5916792 - 1004 SHEFFIELD COURT, WINTER PARK, FL 32792 38 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1764
       Built: 1976   Tax: $265 (2020)
    Community: Howell Estates Rep
    Pool: Yes

    Single Family


    Estimated Monthly Payment: $1,798 (change assumption)
    Mortgage ($1,776) + Taxes in 2020 ($22)

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    Taxes:$265

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle


  • 7789 FOX KNOLL PLACE, WINTER PARK, FL 32792

    $309,0002 Days on yellowkey   MLS ID: O5916762

    For Sale O5916762 - 7789 FOX KNOLL PLACE, WINTER PARK, FL 32792 19 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1629
       Built: 1989
    Monthly Fee: $19
       Tax: $1,247 (2020)
    Community: Bridgewater
    Pool: No

    Single Family


    Estimated Monthly Payment: $1,816 (change assumption)
    Mortgage ($1,693) + Fees ($19) + Taxes in 2020 ($104)

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    Taxes:$1,247

    Elementary School: Eastbrook Elementary

    High School: Lake Howell High

    Tax Year: 2020

    Middle School: Tuskawilla Middle




Why Bother Searching Elsewhere for Winter Park Homes for Sale and Other Real Estate?

Winter Park home, townhome, condo, villa, and other listing sales data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on houses for sale in Winter Park. You can use our website to view Multiple Listing Service (MLS) data on Winter Park Real Estate. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Winter Park listings.



Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, South Broward Board of REALTORS®, MIAMI MLS, JTHS MLS, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2021 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.